Most men have no problem speaking to a woman they've just met as long as they don't actually have to exert the effort involved in initiating the conversation. Unfortunately, this restricts many of the random encounters and great opportunities that would have presented themselves. Let's talk about some of the do's and don'ts for starting a conversation with a woman that catches your eye.

Flow your interruption smoothly with whatever she's doing. If she has her phone out and you're thinking of getting a new one, ask her how she likes it. If she and her friend are having a debate about something, put your two cents in (if they seem friendly and approachable). If she's trying out a new exercise at the gym, ask her what she likes about it.

Obviously, staring at cleavage is a big no-no, but betraying yourself (and your own confidence) by forgoing sustained eye contact (okay, not too long, ya creep!) is a sure way to go home without her number.

You know how in movies they always show a beautiful woman alone at the bar? Beautiful women are never alone at a bar. That means you'll have to speak to her friends. And you know what? That's okay. Being fun and sociable and enjoying whatever situation or conversation you're in has its perks. Also, the woman you are interested in will see that you've hit it off with someone she chooses to spend time with, which is a big plus.

Many women are sweet and wonderful, but there are also manipulative ones out there who know that asking for a drink regardless of their actual interest level in a guy will net them a drink. Buying a woman a drink the first time you meet her (unless it's on a date) is like saying, "Here, this is your payment for having to spend time with me," so you should probably go ahead and skip that tactic. If she asks you to get a drink and you say, "No," she'll either be impressed/attracted to you for not giving in to her immediate desire, or she'll leave your company in search of another guy. Good riddance.

Don't be boring like all the other guys she's passed on. Have an amusing observation, an interesting anecdote or a worthwhile question for her instead of just saying "Hi," "What's up," or "Do you like this place?”

About Jason Epstein...
Jason Epstein is a nationally published freelance writer living in the greater NYC area. He's known for his close friends/good conversations/playing bass/wind in the face/rocking out/reading up/holding it down/good times/turning on dimes/and sometimes trying to
rhyme(s). He can be reached at his website and you can follow him on Twitter here.